Winter Haven / Cypress Gardens Homes for Sale

Winter Haven / Cypress Gardens Homes for Sale

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County, renowned for its picturesque lakes and vibrant community spirit. Known as the “Chain of Lakes City,” Winter Haven boasts over 50 sparkling lakes, offering endless opportunities for boating, fishing, and waterfront recreation. The area is steeped in history and is famously home to the iconic Cypress Gardens, a botanical wonderland that once captivated visitors with its stunning gardens and thrilling water ski shows. Today, the legacy continues with an array of outdoor activities, parks, and family-friendly attractions, making it a perfect place to call home.

As you explore the real estate market in Winter Haven, you'll find a diverse selection of homes for sale that cater to various lifestyles and budgets. From charming single-family homes nestled in friendly neighborhoods to modern townhomes and luxurious waterfront properties, there’s something for everyone. Many homes feature spacious layouts, beautiful outdoor spaces, and easy access to the region's natural beauty. Whether you're looking for a cozy retreat or a vibrant family home, Winter Haven offers a welcoming atmosphere that embraces both tranquility and adventure.

With its ideal location, just a short drive from Orlando and Tampa, Winter Haven provides the perfect balance of small-town charm and big-city convenience. Enjoy the local dining scene, boutique shopping, and community events that bring residents together. Discover your dream home in Winter Haven today, and embrace a lifestyle filled with sunshine, serenity, and endless possibilities!

Newest Winter Haven / Cypress Gardens Homes for Sale

3391 Livingston Way, Winter Haven
$215,000
2 Beds ⋅ 2 Baths ⋅ P4940388 MLS
Welcome to your Florida retreat! This beautifully maintained 2-bedroom, 2-bathroom FURNISHED home offers low-maintenance living in a gated Winter Haven community filled with resort-style amenities! Whether you're searching for a full-time residence or seasonal getaway, this home is ready for you to move right in! Enjoy peace of mind with numerous updates, including a roof approximately 5 years old, NEW A/C February 2026, NEW range 2026, refrigerator approximately 2 years old, microwave 1 year old, and carpeting approximately 5 years old. Spend less time maintaining and more time enjoying Florida! The HOA takes care of exterior painting and front landscaping. Additional included services feature cable TV, internet, grounds maintenance, private roads, community pool, recreational facilities, management, and common area taxes. LOVE THE WATER? Enjoy lake access, community boat ramp, boat slips, dock, fishing, and beautiful waterfront areas! Cruise the neighborhood in your golf cart or enjoy the walking paths and sidewalks. Community amenities include a clubhouse, fitness center, swimming pool, tennis courts, dog park, parks, and gated entry! Conveniently located near shopping, dining, medical facilities, and Central Florida attractions. EXCITING PROPERTY TAX NEWS! With Florida's newly approved Amendment 3, establishing Florida residency by December 31, 2026, may qualify eligible homeowners for expanded homestead tax benefits without the new-resident waiting period! Residency and exemption requirements apply. Why spend another winter wishing you were in Florida? This furnished home offers comfort, convenience, and the Florida lifestyle you've been dreaming of! Schedule your private showing TODAY! Buyer approval and community restrictions apply. Verify HOA benefits, amenity availability, and tax eligibility.

3391 Livingston Way, Winter Haven
4030 Bedford Avenue, Winter Haven
$385,000
4 Beds ⋅ 3 Baths ⋅ O6455218 MLS
Welcome to Resort-Style Living in Traditions! Discover the best of Florida’s active adult lifestyle in this beautiful 4-bedroom, 3-bath home in the highly desirable Traditions community in Winter Haven. This gated, 55+ maintenance-free neighborhood offers true resort-style living on the shores of scenic Lake Ruby. Step inside and enjoy brand-new luxury vinyl plank flooring, creating a fresh, modern feel. Utilize the spacious kitchen with a breakfast nook, a bar, an island, and the option to serve guests in your formal dining room. The home features an oversized enclosed lanai with peaceful nature views - the perfect spot to relax with your morning coffee or entertain friends while watching the Florida wildlife. The primary bedroom has an en-suite bath with a garden tub, dual sinks, and large walk in shower. At the front of the home are a bedroom and bathroom that would make an ideal private retreat for hosting overnight visitors. Then, just off the living area are two additional bedrooms with a jack-and-jill bath. An updated roof gives you added peace of mind for years to come. Beyond your front door, the lifestyle truly shines. Traditions is known for its impressive amenities, including: • A stunning 19,000-square-foot lakefront clubhouse with fitness center, aerobics studio, ballroom, billiards, library, and arts & crafts studio • Resort-style heated pool and spa • Tennis, pickleball, bocce, and shuffleboard courts • Private boat ramp and dock slips on Lake Ruby with access to the Chain of Lakes • Scenic walking paths, dog park, and lakeside gazebo • A full calendar of social events and clubs Best of all, the maintenance-free lifestyle means the HOA takes care of the lawn care and exterior painting, so you can spend your time enjoying the community instead of working on the house. Conveniently located near shopping, dining, medical facilities, Legoland, and easy access to Highway 27, this home puts everything you need within reach while offering a peaceful, active retreat. If you’re looking for low-maintenance living with resort amenities and a welcoming community of active adults, this is the one. Schedule your private tour today and experience the Traditions lifestyle for yourself!

4030 Bedford Avenue, Winter Haven
1783 White Elephant Loop, Winter Haven
$364,900
5 Beds ⋅ 3 Baths ⋅ O6453743 MLS
Virtually Staged. ONLY $1,000 DOWN AT SIGNING! BUILDER PAYS THE REMAINING CLOSING COSTS! PLUS, A PROMOTIONAL 4.99% INTEREST RATE FIXED FOR THE FIRST 5 YEARS WITH A 5/1 ARM FOR QUALIFIED BUYERS! BRAND NEW, MOVE IN READY SINGLE FAMILY HOME WITH 5 BEDROOMS AND 3 FULL BATHROOMS! Why wait months to build when you can move right into a beautifully designed new construction home with incredible builder incentives? Welcome to 1783 White Elephant Loop, featuring the spacious Spring floor plan by LGI Homes in the desirable Peach Crossings community. This impressive home offers five generously sized bedrooms, three full bathrooms, and a thoughtfully designed layout that combines modern comfort, functionality, and plenty of room to grow. Step inside to discover bright, inviting living spaces perfect for everyday living and entertaining. With five spacious bedrooms, you'll have endless possibilities for a home office, guest accommodations, playroom, fitness room, or hobby space. The exceptional owner's suite provides a relaxing private retreat with plenty of room for a king sized bed, additional furnishings, and a cozy reading area. The adjoining bathroom features a beautiful dual sink vanity, convenient linen closet, and an impressive walk in closet offering abundant storage and organization. Three full bathrooms provide added convenience for busy households and visiting guests. Enjoy the benefits of brand new construction, modern finishes, and the peace of mind that comes with owning a newly built home. Peach Crossings offers a welcoming community atmosphere with a children's playground and picnic area, along with convenient access to nearby schools, shopping, dining, and everyday essentials. Whether you're looking for additional bedrooms, flexible living spaces, or a beautiful new home without the construction wait, this property checks all the boxes! With builder paid closing costs, incredible promotional financing, five spacious bedrooms, and immediate move in availability, this is an outstanding opportunity to own brand new construction at an exceptional value. Schedule your private showing today! Promotional financing and closing cost incentives are subject to buyer qualification, participating lender requirements, and program availability. The advertised 4.99% interest rate applies to the initial five year fixed rate period of a 5/1 adjustable rate mortgage, after which the rate may adjust.

1783 White Elephant Loop, Winter Haven
100 Alachua Drive, Winter Haven
$495,000
3 Beds ⋅ 2 Baths ⋅ L4966310 MLS
MAIN HOME PLUS TWO INCOME-PRODUCING STUDIO APARTMENTS – $1,800 IN MONTHLY RENTAL INCOME! Looking for a property that offers more than just a place to call home? This unique property features a main residence plus two studio apartments currently rented for a combined $1,800 month! Situated on an oversized, fully fenced double corner lot, this property offers incredible flexibility and income potential. With its convenient location near LEGOLAND Florida and Winter Haven’s famous Chain of Lakes, there is also exciting potential for short-term rentals or Airbnb opportunities. Enjoy the Florida sunshine in your private 15’ x 30’ screened-in pool or unwind in the hot tub. Inside the main home, you’ll find a beautifully updated kitchen and bathrooms, luxury vinyl plank flooring throughout, newer windows, and a versatile bonus room that could easily serve as a fourth bedroom. There’s plenty of room for vehicles with a triple-wide concrete driveway and paved parking for approximately 10 cars. Additional features include an RV hookup, fully paid-off solar panels to help reduce electric costs, a large storage shed, portable generator hookup, and the possibility of adding a detached garage. Best of all, NO HOA! Whether you’re looking for additional rental income, multigenerational living, or a property with room to grow, this move-in-ready home offers flexibility, convenience, and plenty of possibilities. Live in one, rent the others, and let your property work for you! Don’t miss this unique Florida lifestyle opportunity!

100 Alachua Drive, Winter Haven
3123 Laurel Oak Ln, Winter Haven
$315,000
4 Beds ⋅ 2 Baths ⋅ P4940376 MLS
Short Sale. A Must-See! Beautifully designed 4-bedroom, 2-bathroom home with a 2-car garage, presenting 1,983 square feet of living space with a bright and airy open floor plan and high ceilings. Perfect for families or anyone who loves to entertain, this home seamlessly blends style, comfort, and functionality. The kitchen boasts ample counter space, a breakfast bar, stainless steel appliances, solid wood cabinets, and even a pantry. Strategically located just off the kitchen, the laundry room offers additional storage space. Enjoy gorgeous, durable vinyl flooring throughout the main living areas and cozy carpet in the bedrooms for ultimate comfort. The expansive primary bedroom highlights a walk-in closet and en suite bathroom complete with a double vanity and large step-in shower. The welcoming, screened-in front porch and lovely landscaping provide great curb appeal. Step out back through sliding glass doors to a second screened porch overlooking the fenced-in backyard, great for relaxing, weekend gatherings, or enjoying your morning coffee. Located in Villamar! Low annual HOA fee; the amenities include a community pool at the main entrance of the neighborhood on Cunningham Dr., along with a playground. This pristine home is ready to welcome its next owners. Don't miss the opportunity to make this beautiful home yours!

3123 Laurel Oak Ln, Winter Haven
188 Morning Dew Court, Winter Haven
$295,000
3 Beds ⋅ 2 Baths ⋅ O6455368 MLS
Virtually Staged. Welcome to 188 Morning Dew Court, where comfort, style, and the Florida lifestyle come together in the gated Winterset community! Nestled on a quiet cul-de-sac, this Mediterranean-style home offers 3 spacious bedrooms, 2 bathrooms, a 2-car garage, and 1,730 square feet of thoughtfully designed living space. Step inside to discover an inviting open-concept floor plan featuring soaring vaulted ceilings, beautiful oak wood flooring, and abundant natural light. The spacious living area flows seamlessly into the kitchen, complete with granite countertops, ample cabinetry, and a charming breakfast nook. A separate dining area provides additional space for entertaining. The desirable split-bedroom layout offers added privacy, with a generous primary suite featuring a walk-in closet, dual vanities, a relaxing jacuzzi garden tub, and a separate walk-in shower. Two additional bedrooms provide flexibility for guests, a home office, or hobbies. Enjoy Florida's beautiful weather from your enclosed rear lanai. But the lifestyle doesn't stop at your front door! Morningside at Winterset offers outstanding community amenities, including a clubhouse with lounge, swimming pool, hot tub, tennis courts, pickleball courts, and shuffleboard. Love the water? Residents enjoy a private community boat ramp and fishing pier on Lake Winterset, providing access to Winter Haven's renowned Chain of Lakes. Whether boating, fishing, relaxing poolside, or enjoying a friendly game of pickleball, there's something for everyone! Conveniently located near shopping, dining, entertainment, and LEGOLAND Florida Resort, this home offers a wonderful combination of tranquility and convenience. Why settle for just a home when you can enjoy an entire resort lifestyle? Schedule your private showing today!

188 Morning Dew Court, Winter Haven
2097 Whispering Trails Boulevard, Winter Haven
$410,000
4 Beds ⋅ 3 Baths ⋅ O6455563 MLS
Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 10 minutes from the exciting attractions of Legoland, and less than an hour from the Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and amenities. This charming home comes move-in ready, including all essential appliances such as a range, refrigerator, microwave, garbage disposal. The secure, gated community offers peace of mind and added privacy, making it an ideal place to call home. Whether you're looking for a primary residence, vacation home, or investment property, this residence offers comfort, convenience, and easy access to some of Florida’s top attractions. Don’t miss your chance to own this fantastic 4 bed 3 full bath pool home in the fast-growing City of Winter Haven!

2097 Whispering Trails Boulevard, Winter Haven
135 Eloise Oaks Drive, Winter Haven
$365,000
3 Beds ⋅ 2 Baths ⋅ L4966272 MLS
Remarkable 3-bedroom, 2-bathroom single-story home offering 1,866 square feet of comfortable living space on a spacious 1/4 acre lot in Winter Haven, FL. This meticulously maintained residence is packed with features designed for both comfort and style. The large kitchen is well designed for organization with granite countertops, built-in sliding drawers, and sleek stainless steel appliances. Throughout the home, you'll find elegant tray ceilings that add a touch of sophistication to the living spaces. For your peace of mind, the property is equipped with an ADT security system and a state-of-the-art Ultraviolet AC Air Purification Scrubber system, ensuring the cleanest indoor air quality for you and your family. The living area opens up to a COZY SCREENED LANAI complete with sliding windows, making it the perfect spot for year-round relaxation. Step outside to discover an entertainer's dream outdoor space featuring an EXTENDED PAVER PATIO with an elevated grilling station. The FULLY FENCED YARD provides privacy. Located in the quiet Eloise Oaks neighborhood, this home is just up the street from LAKE ELOISE, one of many lakes in the renowned Winter Haven Chain of Lakes. You'll be just minutes from LEGOLAND Florida Resort and perfectly positioned between Florida's beautiful east and west coasts as well as the Orlando attractions. This exceptional home combines comfort, style, and an unbeatable location. Schedule your showing today!

135 Eloise Oaks Drive, Winter Haven
463 Daisy Lane, Winter Haven
$259,900
2 Beds ⋅ 2 Baths ⋅ L4964181 MLS
SELLER IS OFFERING $2,500 IN CONCESSIONS!!! This well maintained Lake Daisy Estates home located in southeast Winter Haven. This 2 bedroom & 2 bathroom home is ready for its new owners. Recent Upgrades: Roof and Solar (2023), SELLER WILL PAY OFF SOLAR PANELS AT CLOSING!!! Windows and Sliding Glass Door are Renewal By Andersen (2024), retractable garage door screen (motor replaced 2026). Enjoy your 2-car garage with the door open and the mosquitoes kept out! Only ten homes on the street provides a great space for playing outside, walking, bike riding and more! Very low traffic as other roads lead to community entrances/exits! NO HOA FEES! NO CDD FEES! Electric bill for October usage was less than $17!!! The paid off solar system provides the potential to SAVE HUNDREDS OF DOLLARS EACH MONTH FOR THE LIFE OF THE SYSTEM!!! This property is ready for the new owners to make it their own. Lake Daisy Estates is approximately 1/2 mile from A rated Garden Grove Elementary School, 1 mile from the Street Audubon Nature Center, 1 1/2 miles from Wal-Mart, 2 miles from Advent Emergency, 3 miles from Publix, 4 miles from Home Depot and 5 miles to Lowe's. This home is centrally located in Florida and is approximately 50 miles from Orlando International Airport and 60 miles from the Tampa International Airport. Don’t miss out, schedule your private showing today!

463 Daisy Lane, Winter Haven
4000 Giorgio Drive, Winter Haven
$325,000
4 Beds ⋅ 3 Baths ⋅ TB8557851 MLS ⋅ Meritage Homes BLDG.
Brand new, energy-efficient home available by Dec 2026! First-floor primary suite ensures everyone has their own private space. Second floor offers a spacious loft that can be used to best fit your family's needs. Enjoy preparing meals with your family in the open kitchen with spacious work island. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

4000 Giorgio Drive, Winter Haven
5378 San Pietro Drive, Winter Haven
$396,828
5 Beds ⋅ 3 Baths ⋅ TB8564826 MLS
Under Construction. Valencia BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender.  Prepare to be impressed by the Valencia, a two-story home featuring 5 bedrooms, 3 bathrooms, and a 2-car garage. This floorplan is designed for modern living and effortless entertainment. Step through the elegant foyer into a vibrant main living area, complete with a private guest suite for ultimate comfort. The kitchen shines with sleek quartz countertops, stainless steel appliances, and luxurious vinyl plank flooring overlooking the dining area which flows beautifully to the covered lanai through sliding glass doors. Upstairs, you’ll find the secluded owner’s suite complete with a walk-in shower, dual vanity and spacious walk-in closet. Conveniently located by the additional bedrooms is the cleverly designed oversized laundry room. Another modern feature of the Valencia is the smart thermostat with voice control, making energy efficient living a breeze. Outside, enjoy the chic elevation and professionally curated landscaping that adds the perfect finishing touch to this exceptional home. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5378 San Pietro Drive, Winter Haven
5357 San Pietro Drive, Winter Haven
$329,990
4 Beds ⋅ 3 Baths ⋅ TB8564820 MLS
Under Construction. Turquesa BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender.  The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.   Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5357 San Pietro Drive, Winter Haven
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